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So you want to work for a startup

4 min read

Recently, I’ve chatted with a bunch of designers who’ve said they’re interested in working for startups. Several have asked me if I have any advice, so I decided to write a quick post about the things I’ve learned over the course of my last 9 years in the startup industry.

The key to making a successful jump into a startup: first define exactly what it is you value in a workplace.

It dawned on me early in my career that I don’t love working for startups in general, I love working for my startups because they fit my lifestyle and personality.

There are a series of questions you need to ask yourself to know if a particular startup is right for you:

1. What is the startup’s view on work-life balance?

I’m a mom, and it’s important for me to be able to work remotely, either on occasion or full time. Days when my kiddo is running a fever and can’t go to school, she can lay on the couch next to my desk sleeping while I work. I don’t lose any productivity by having to take a sick day, and my team still meets our deadlines. And we utilize a set of fabulous communication tools like Slack that let us communicate as clearly (or even more clearly, to be honest) as we would in a traditional office. I’m fortunate to work for a fully distributed company now that is very family centric.

Other startups require extremely long hours in the office and 100% dedication to the job—to the point that there basically isn’t room for anything else in your life. Tons of people love and feed off of that intensity.

Often times people join a startup expecting scenario A, but instead they wind up in scenario B and feel like they’re drowning. Make sure a startup’s work-life balance is a good fit for your lifestyle and personality before you sign on the dotted line.

“Before you join a startup, know their view on work-life balance.”

2. Do they have a benefits package that suits your needs?

Some startups invest tons of money in benefits packages to attract talent, others advertise hefty starting salaries with little-to-no benefits, and still others have no benefits and low salaries, but they offer stock options. The list of scenarios goes on, but what it really comes down to is whether they offer what you need. (Then you get the rare few like InVision that offer all of the things. Check out the open positions here.)

3. Is the company working on something you’re passionate about?

This is extremely important. When you join a startup, you need to be excited about what you’re working on, because things can get crazy. If you’re not committed to the product, you’ll never make it through the rapid growth stage.

When you jump into a startup environment, you’re kind of jumping into a casino situation. You’re betting your salary that the company is going to take off and soar. Just as it goes with gambling, though, there’s a chance that the company is going to flop—and more often than not with startups, this is the case. (I’ve been super fortunate to land in 2 extremely successful startups back to back.)

Take a hard look at the company, their values, their long-term plans, and how passionate their senior leadership and employees are about making magic happen. Then evaluate whether you’re passionate enough about the company and the product to take the gamble.

4. Does the company have room for career advancement?

One of the coolest things for me about working for the startups I’ve worked for has been the opportunity for cross-departmental career advancement. At my last startup we had folks who came into the company as entry level in a department where they fit, only to discover they had serious passion for another area of the company. They didn’t need to quit to have the opportunity to advance their careers in that totally different direction because the company did a ton of hiring and promotion from within.

When you join some startups in the early stages, you end up wearing tons of hats. Be prepared to do all kinds of things that “aren’t in your job description.” The neat thing about those environments is that once the company starts to grow, you can sometimes work with the senior staff to carve your own niche and focus on the portions of the job you enjoyed most (but that’s not always the case).

“Not committed to the product? You’ll never make it through the rapid growth stage.”

There are other startups that take a “once you’re in a position, you’re stuck there” approach and they hire externally for the most part. Think about your career goals, and look into the ability to move within the organization you’re considering to make sure you’re aligned in those areas.

5. Do these people seem like folks you’d enjoy spending time with/feel inspired by/trust with your career and could turn into a work family?

Some people are going to read that work family line and think it’s lame. But in all seriousness, when you’re working at a startup you spend a huge amount of time with a small group of people. While differing opinions are great because they often lead to killer innovation, the ability to get along as a group after sharing those differing opinions is huge.

You need folks who are all on the same page and are borderline obsessed with making your company succeed, and who are willing to do whatever needs to be done in order to make that dream happen. Being able to collaborate doesn’t mean being similar, or all thinking the same way (your life would be horribly boring, as would your products, if your whole team were made up of clones of you)—it just means being able to communicate in a productive way in a fast-paced, intense environment. Make sure the team you’re interviewing with feels like a good culture fit for you before you dive in.

If you’re aligned on all of these points and decide to go for it, get ready for an incredibly exciting roller coaster ride that may lead to dreams becoming reality.

Or the ride may fly off the track and crash and burn. But that’s the fun in working for a startup, right? The excitement is in the gamble.